


All Too Well // D.W

by lilyanderson



Series: All Too Well // D.W [1]
Category: Supernatural
Genre: Alternate universe Supernatural, Eventual Smut, F/M, Implied Sexual Content, Mild Sexual Content, Slow Burn, Supernatural AU - Freeform, dean winchester au
Language: English
Status: In-Progress
Published: 2020-11-27
Updated: 2020-11-27
Packaged: 2021-03-09 18:55:38
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,950
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27731137
Author URL: https://archiveofourown.org/users/lilyanderson/pseuds/lilyanderson
Summary: Supernatural AU // Bailey Walker has spent the last year picking up the pieces of her failed relationship. Just when she thinks she is almost whole again, the rug is pulled from underneath her yet again. Her life is a mess, she's a mess, and yet throughout it all, she finds herself growing close to somebody she's spent eight years pushing away. Bailey can feel Dean worming his way back into her life and consequently her heart, but she's been burned before, can she find it in herself to trust him again?
Relationships: Dean Winchester/Original Female Character(s), Sam Winchester/Original Female Character(s)
Series: All Too Well // D.W [1]
Series URL: https://archiveofourown.org/series/2028457
Kudos: 4





	All Too Well // D.W

**“J** ess can you please stop that?”

The infuriating sound of paper flapping, which had Bailey’s clenching her hands so tightly that her fingernails were leaving crescent shaped indentations on her palm, immediately ceased. The pain was only a minor inconvenience in comparison to the unbearable, choking humidity that had turned her tiny apartment into a temporary sauna.

“I can’t help it,” Jess said with a whine, unable to resist the temptation of fanning herself and picking the newspaper back up, “maybe if you fixed your AC, I wouldn’t have to.”

Bailey, in a fit of pure frustration, pulled her sweat soaked shirt over her head in a futile attempt at cooling herself down. The heat plaguing her apartment had Bailey willing to do just about anything to escape it, and that didn’t exclude stripping off in-front of her best friend.

“I already told you, my AC doesn’t need fixing.” Bailey quipped, the sticky heat making her more irritable than usual as she dragged herself into the kitchen in search of something, _anything_ , that would cool her down.

Unfazed at her best friend’s state of undress, Jess rolled her eyes at Bailey’s ongoing determination that her AC was in fact not broken; even though it had all the effect of an old asthmatic man standing in the corner breathing on them. It was beyond her that somebody who hated the heat so vehemently, would be so opposed to the idea of fixing the one thing that would cool her apartment down.

“You could just ask Dean—”

Bailey, who had found a bottle of water shoved at the very back of the fridge and had been just about to down it, whipped around so fast that she was worried she may get whiplash.

“ _No_.”

“Oh, come on,” Jess said exasperatedly, hands on her hips, “he isn’t _that_ bad. And he’ll probably do it for free.”

“Yes, Jess, he is _that_ bad. I’d rather pay somebody than have that man in my apartment.”

Jess grinned, “Ah, so you admit you need somebody to fix it.”

Scowling in her best friend’s direction, Bailey opened the bottle and chugged half of the icy cold liquid in one go, instead of coming up with a sarcastic retort like she wanted to.

“So, I need to tell you something,” Jess said slowly, hesitating as she watched in amusement whilst Bailey chugged the water and simultaneously shimmied her sweaty denim shorts down her legs, “Bails, if you were gonna strip for me, you could have at least worn matching underwear.”

If it were anybody else, that comment would have her cheeks burning read and stuttering. But Jess had seen Bailey in much worse states, and vice versa, to the point where they would have to do something really scandalous for either of them to bat an eyelid.

“You would be lucky to have me strip for you, Hello Kitty briefs and all."

Choosing to put an end to the exchange, Jess cleared her throat and continued with what she had been waiting – no, _dreading_ – to say, “So, there’s no easy way to say this and I’m just going to come right out and say it. Sam invited Chris to the wedding, and well, he’s RSVP’d.”

The revelation came with a grimace, as though she’d just ignited an explosive and was waiting for the big show.

“And?” Bailey asked, as though waiting for another part to the story.

Jess raised an eyebrow, perplexed by her seemingly blasé attitude towards the news. "And you're okay with that?"

Bailey faltered at that; she knew in her mind she wasn’t okay. She hadn’t been okay in a very long time, but it had always been so easy to pretend otherwise when everybody around her were so terrified of even mentioning her ex-boyfriend’s name.

Almost a year had passed since their three-year relationship had come to an end, but Bailey was still stuck in the same cycle of going to work, faking wholesome smiles and conversation with customers, pretending that she didn’t feel like her whole life was crumbling around her, and then coming home to an empty apartment to mourn a life she almost had.

One day Bailey would look back and feel nothing but embarrassed at the thought of all the time she’d spent grieving a relationship that was long since over. But that day didn’t seem to be on the near horizon.

Forcing her lips to curve up into something that resembled more of a grimace than a smile, Bailey finally spoke, “Yeah, I’m okay with it. It’s just one day, and besides, it’s your guys’ day, not mine. You deserve to have whoever you want there.”

In the back of her mind, Bailey knew she couldn’t have expected Sam not to invite Chris. They’d been best friends at one point, maybe not so much anymore but they were still friends, and so it was no shock that he would be invited.

Despite noticing the way Bailey’s hazel eyes looked slightly glassy and the hesitation before she responded, Jess chose not to push the subject. She’d witnessed first-hand what she had gone through when Chris left, and for her best friend’s sake, she didn’t want to cause the kind of breakdowns that she’d spent six months coaxing Bailey out of.

Jess had spent far too many hours watching Bailey sob, barely able to breathe through the tears because of what Chris had done to her, and she refused to be the person who brought those memories back up.

“Hey, how about you put on some new clothes and we go get a beer at the Roadhouse?”

And with that, normalcy was injected back into the room.

***

“There’s my girls.”

Bailey and Jess were both grinning from ear to ear as they approached the bar, squeezing their way through the people crowded around the pool table, where Ellen was already preparing their drinks. A bottle of beer and a tequila shot each were waiting for them when they finally made it to their favourite bartender.

Without hesitation, Bailey down the gold liquid, barely flinching as it burned its way down her throat. The concerned look Jess shot her didn’t go unnoticed as they both took their seats, but she chose to ignore it in favour of greeting Ellen.

“Bad day?” Ellen asked, watching with a glint in her eye as Bailey chugged half of her beer in one go.

Heaving out a heavy sigh as she placed the bottle back down onto the bar, “You could say that,” she said, letting her eyes glance around the room, grinning as she spotted Jo at the pool table, clearly beating her flustered looking opponent.

Although there was a three-year age gap between them, Bailey and Jo had always been close friends, all but growing up together. Circumstance had brought them together, their parents were all good friends and Bailey had been coming to the Roadhouse for as long as she could remember, but their friendship had stood the test of time.

And then came along Jess, who just slid so easily in with them, that it felt like they’d all always been friends.

Catching her eye, Bailey sent a wink to Jo, who shot one straight back at her, before focusing back up on her game.

“Is Sam swinging by, too?” Ellen casually asked Jess, as she absentmindedly wiped at the bar with a rag.

“Probably,” Jess said, taking a sip of her beer, “if Dean has anything to say about it.”

Bailey couldn’t help the involuntary eye roll that came from the mention of Dean. It was an understatement to say that she wasn’t his biggest fan, but the words that she had to describe her feelings towards him were very unsavoury.

Along with Jo, Bailey had grown up with Sam. Dean being four years older than them, she never really saw him as anything other than an annoying older brother, who enjoyed teasing the hell out of all three of them whenever he got the chance.

But that had all changed during the summer after she and Sam had graduated high school. Something shifted between Bailey and Dean – Dean no longer seeing her as just his brother’s irritating best friend, and Bailey spurred on by raging teenage hormones. Neither of them had seen the mutual attraction coming, but there was nothing stopping it.

They fell into what could be best described as a summer fling, because by the time September came and Bailey was off to college, it all came crumbling down. By then, she had developed some real feelings for him – beyond just wanting to jump his bones every time he walked through the door – but in classic Dean fashion, ever afraid of making genuine connections with women, he blew her off with a text message. And that was that.

Eight years later, Bailey still held a grudge on the older Winchester.

“Speak of the devils.”

Draining the last of her bottle, Bailey couldn’t help the eyebrows that pinched into a frown as she turned to see the two brothers walking through the front door, laughing loudly at something. Sam was still dressed in his office suit, but Dean had changed out of his usual work navy overalls, into a pair of blue jeans and a red flannel shirt.

_He looked good._

Bailey immediately mentally cursed herself as soon as the thought entered her head. It frustrated her to no end that even though all she felt for the older brother was revulsion, she couldn’t deny the glaringly obvious fact – Dean Winchester was a sight to behold.

Whilst Jess got up to greet her fiancé, Bailey turned back to the bar and ordered another beer and a few more shots of tequila. She would need them if she were going to get through an evening with him.

As Ellen placed the shots of tequila onto the bar, a hand reached over from behind Bailey and took one. She didn’t need to look to know who it was – there was only one person on the planet who would have the nerve.

“For me? You shouldn’t have, sweetheart.”

“You’re an ass.” Bailey said, though lacking in her usual conviction, too fed up to entertain the little feud they had going. She took another shot without looking at him, hoping he would take the hint to leave her alone

Much to her chagrin, Dean sat down next to her, signature smirk as he looked over at her, before turning his attention to Ellen.

“Two beers and a whiskey, please.”

“Coming up, doll.”

Dean opened his mouth to speak, but whatever inevitably provoking words he was going to say died on his tongue as Sam and Jess finally joined them; Sam hugging Bailey from behind, swiftly pressing a kiss to her temple, a quiet sorry whispered into her auburn hair before pulling away.

Bailey sent him a look that said he had nothing to be sorry for, but she knew that no matter what she said or did, Sam was going to feel guilty for inviting Chris. It did make her think why invite him if he felt so bad about it, but she had no urge to question it.

The three of them began chattering around Bailey, but she wasn’t listening. She could barely focus on the sound of the Led Zeppelin song blaring through the stereo, let alone whatever her friends and Dean were talking about.

Although she’d put on a brave face, the mention of Chris earlier had really floored her. It had been a year since he walked out of her life, eyes set on bigger and better things – things Bailey apparently couldn’t offer him – and yet one mention of his name and she felt like she was back to square one.

It occurred to her on many occasions that Chris was as good as it got for her. Although not her first love, the infuriating lady-killer knocking whiskey back beside her frustratingly held that title, she really thought that he was going to be it. She saw a life with him, a good life, that she couldn’t picture ever having with anybody else.

So, was that it? Was she destined to a life of loneliness and forever picking up the pieces of a life she never got to have? Those kinds of questions often kept Bailey awake at night – more often than she’d care to admit.

Her uncharacteristically quietness didn’t go undetected by any of them – even Dean was eyeing her with an expression that could be described as mild concern. Normally she’d be at the centre of the conversation, cracking jokes, ribbing on Sam for wearing his monkey suit at the bar.

“Hey, Bails, up for a game of pool?” Sam asked, pulling her out of whatever daydream she had been caught up in.

Almost as though she was suddenly remembering where she was, Bailey blinked a few times before turning to him with a mischievous smile, “Only if you’re looking to get your ass kicked.”

The smile didn’t quite reach her eyes and there wasn’t the usual skip in her step as she and Sam walked over to the vacant pool table – Jo now helping her mother behind the bar as the usual Friday evening crowd began filling up the building.

“Bails,” Sam started once they reached the table, away from prying ears, “you know I didn’t want to upset you, right?”

Picking up her pool cue and starting to chalk the end of it, she nodded, trying to look as unfazed as possible. When Sam had asked her for a game, she knew he just wanted to get her away from the other two so that he could say his piece.

“I’m not upset, Sam,” she said with a sigh, “you have every right to invite whoever you want to your wedding, okay? Please, can we just leave it there for now?”

“Right, yeah, sorry.”

“So, you ready to get your ass kicked?” Bailey taunted with a grin, the tension immediately dissipating into nothing.

“Bring it.”

Ten short minutes later, Bailey had her cue above her head, yelling out in triumph at her win. Sam, though shaking his head at her less than subtle display of victory, grinned along with her. He was simply happy that she was acting more like herself, but for how long he didn’t know.

“Another?” she asked, setting the balls back into the rack in the middle of the table.

Sam huffed out a laugh. “Sure, you set up, I’ll go get us another drink.”

By now, Bailey was feeling buzzed, the two beers and however many shots of tequila had started to kick in. She could handle her alcohol reasonably well and it would take a lot more for her to be truly drunk, but she was getting that warm fuzzy feeling in the pit of her stomach and she swayed slightly as she walked around the table.

Maybe it wasn’t the best way to cope, but the numbing effects of alcohol seemed to be working well to take her mind away from Chris.

A somewhat pleasant mood had begun to settle over Bailey, and only improved throughout the night. Being around her friends – Jess, Sam, Jo, even Charlie had made an appearance – was all the therapy she needed.

She had beaten Sam at another few games of pool before they decided to call it quits, settling instead in their usual booth at the far corner of the bar, away from the noisy patrons. The rest of their friends had slowly joined them, bringing over more drinks that only served to get Bailey increasingly buzzed.

Bailey and Charlie were clinking their shot glasses together, before knocking them back, when Dean approached the table. Before that, he’d been chatting up a pretty little blonde at the bar – as per usual, searching for somebody to take home. It wasn’t a night at the Roadhouse if Dean didn’t leave with a girl hanging off his arm.

But there he was, squeezing himself into the booth, directly next to a disgruntled looking Bailey.

“Luck out?” she asked, eyebrows pinching together when he slings his arm across the seat behind her. He was too close for comfort, his jean covered thigh pressing up against her bare leg.

He shrugged, taking a long pull of his beer. “She has a boyfriend.”

“I’m surprised that stopped you.”

“I do have morals, sweetheart.”

“Could have fooled me.”

Not taken aback in the slightest by her comment, Dean grinned, eyes twinkling with amusement – unlike Bailey, he enjoyed their banter. “You say the sweetest things to me.”

Choosing to ignore the green-eyed man next to her, Bailey tuned back into the conversation. Charlie, Jo, and Jess were chatting about the bachelorette party planned for the following weekend, whilst Sam was completely zoned out, scrolling on his phone.

“Are we still starting at Bailey’s?” Charlie asked, looking over at the girl in question.

“Only if she gets her AC fixed.” Jess replied, grinning smugly over at her.

“I am not having this conversation again, Jessica.”

Dean, who had surprisingly been listening to the conversation, piped in. “I could take a look at it for you.”

Grinding her teeth and clenching her fists, Bailey knew she had been cornered. There was no reasonable excuse to say no to Dean, who was so generously offering his services in front of everybody. Looking over at Jess, who was still wearing the smug grin, she knew her best friend had planned this.

“I’m sure you have plenty of other things to do, I’ll be fine.”

“Nonsense,” Dean said, starting to catch onto Bailey’s hesitation, “I’ll swing by tomorrow afternoon and take a look.”

“ _Great_.”


End file.
